Sodium Carbonate → (2Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine
Reaction equation
C([O-])(=O)C.[K+].Br[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:15]=1)=[N:12][O:13][N:14]=2.C(=O)([O-])[O-].[Na+].[Na+].Br[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[N:25]([CH3:27])[CH3:26]>CN(C=O)C.O>[N:14]1[O:13][N:12]=[C:11]2[CH:15]=[C:7]([C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[N:25]([CH3:27])[CH3:26])[CH:8]=[CH:9][C:10]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
523 mg (1.65 eq.) bis(pinacolato)diboran, 552 mg (4.5 eq.) potassium acetate and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 are added to a solution of 373 mg 5-bromo-benzo[1,2,5]oxadiazole in 8 mL DMF and heated to 80° C. under continuous stirring for 6 hours. 662 mg (5 eq.) sodium carbonate in 3.3 mL water are added together with 500 mg (1 eq.) 2-bromo-N,N-dimethylaniline and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 to the reaction mixture, which is stirred for another 18 hours at 80° C., cooled to room temperature and extracted with ethyl acetate and water. The combined organic phases are washed with brine, dried over magnesium sulfate and evaporated. The residue is column chromatographed (hexane, then hexane/ethyl acetate 8:1) to yield the desired product as an orange resin. MS(ES+): 240 (M+1).
Workup
- stirringis stirred for another 18 hours at 80° C.
- temperaturecooled to room temperature
- extractionextracted with ethyl acetate and water
- washThe combined organic phases are washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customchromatographed (hexane
Sources & evidence
- ORD record
- ord-84c49cd67ec942568ab3dc4c0b137042
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632851B2
Reaction notes
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